JP4323935B2 - Organic light emitting device - Google Patents
Organic light emitting device Download PDFInfo
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- JP4323935B2 JP4323935B2 JP2003406967A JP2003406967A JP4323935B2 JP 4323935 B2 JP4323935 B2 JP 4323935B2 JP 2003406967 A JP2003406967 A JP 2003406967A JP 2003406967 A JP2003406967 A JP 2003406967A JP 4323935 B2 JP4323935 B2 JP 4323935B2
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Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/658—Organoboranes
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
Description
本発明は、新規な有機化合物を用いた有機発光素子に関する。 The present invention relates to an organic light-emitting device using a novel organic compound.
有機発光素子は、陽極と陰極間に蛍光性有機化合物または燐光性有機化合物を含む薄膜を挟持させて、各電極から電子およびホール（正孔）を注入することにより、蛍光性化合物または燐光性化合物の励起子を生成させ、この励起子が基底状態にもどる際に放射される光を利用する素子である。 An organic light-emitting device has a fluorescent compound or a phosphorescent compound by injecting electrons and holes from each electrode by sandwiching a thin film containing a fluorescent organic compound or a phosphorescent organic compound between an anode and a cathode. This is an element that utilizes the light emitted when the exciton is generated and the exciton returns to the ground state.
１９８７年コダック社の研究（非特許文献１）では、陽極にＩＴＯ、陰極にマグネシウム銀の合金をそれぞれ用い、電子輸送材料および発光材料としてアルミニウムキノリノール錯体を用いホール輸送材料にトリフェニルアミン誘導体を用いた機能分離型２層構成の素子で、１０Ｖ程度の印加電圧において１０００ｃｄ／ｍ2程度の発光が報告されている。関連の特許としては，特許文献１〜３等が挙げられる。
In 1987, Kodak Research (Non-patent Document 1) used ITO for the anode and magnesium silver alloy for the cathode, an aluminum quinolinol complex for the electron transport material and the light emitting material, and a triphenylamine derivative for the hole transport material. It has been reported that light emission of about 1000 cd / m 2 at an applied voltage of about 10 V has been reported with an element having a function separation type two-layer structure. Examples of related patents include
また、蛍光性有機化合物の種類を変えることにより、紫外から赤外までの発光が可能であり、最近では様々な化合物の研究が活発に行われている。例えば、特許文献４〜１１等に記載されている。 In addition, by changing the type of the fluorescent organic compound, light emission from ultraviolet to infrared is possible, and recently, various compounds have been actively researched. For example, it describes in patent documents 4-11.
近年、燐光性化合物を発光材料として用い、三重項状態のエネルギーをＥＬ発光に用いる検討が多くなされている。プリンストン大学のグループにより、イリジウム錯体を発光材料として用いた有機発光素子が、高い発光効率を示すことが報告されている（非特許文献２）。 In recent years, many studies have been made on using phosphorescent compounds as light emitting materials and using triplet state energy for EL light emission. A group of Princeton University reports that an organic light emitting device using an iridium complex as a light emitting material exhibits high luminous efficiency (Non-Patent Document 2).
さらに、上記のような低分子材料を用いた有機発光素子の他にも、共役系高分子を用いた有機発光素子が、ケンブリッジ大学のグループ（非特許文献３）により報告されている。この報告ではポリフェニレンビニレン（ＰＰＶ）を塗工系で成膜することにより、単層で発光を確認している。共役系高分子を用いた有機発光素子の関連特許としては、特許文献１２〜１６等が挙げられる。 Furthermore, in addition to the organic light-emitting device using the low-molecular material as described above, an organic light-emitting device using a conjugated polymer has been reported by a group of Cambridge University (Non-Patent Document 3). In this report, light emission was confirmed in a single layer by forming a film of polyphenylene vinylene (PPV) in a coating system. Patents 12 to 16 and the like can be cited as related patents of organic light emitting devices using conjugated polymers.
このように有機発光素子における最近の進歩は著しく、その特徴は低印加電圧で高輝度、発光波長の多様性、高速応答性、薄型、軽量の発光デバイス化が可能であることから、広汎な用途への可能性を示唆している。 As described above, recent advances in organic light-emitting devices are remarkable, and their features are high brightness, variety of emission wavelengths, high-speed response, low profile, and light-emitting devices with low applied voltage. Suggests the possibility to.
しかしながら、現状では更なる高輝度の光出力あるいは高変換効率が必要であり、かつ長時間の使用による劣化等の耐久性の面で未だ多くの問題がある。これらの問題を解決するための手段の１つとして、優れた電子輸送材料を用いることが挙げられる。 However, at present, further high luminance light output or high conversion efficiency is required, and there are still many problems in terms of durability such as deterioration due to long-term use. One means for solving these problems is to use an excellent electron transport material.
電子輸送材料として、アルミニウムキノリノール錯体、フェナントロリン化合物、オキサジアゾール化合物またはトリアゾール化合物などが知られている。これらの化合物を有機発光素子に用いた例として、特許文献１７〜１９などが挙げられるが、電子輸送層として用いた際の特性は十分なものではない。 As an electron transport material, an aluminum quinolinol complex, a phenanthroline compound, an oxadiazole compound, a triazole compound, or the like is known. Examples of using these compounds in organic light-emitting devices include Patent Documents 17 to 19, but the characteristics when used as an electron transport layer are not sufficient.
本発明の目的は、特定なカルボラン化合物を用い、極めて高効率で高輝度な光出力を有する有機発光素子を提供することである。また、極めて耐久性のある有機発光素子を提供することである。さらには製造が容易でかつ比較的安価に作成可能な有機発光素子を提供することである。 An object of the present invention is to provide an organic light emitting device using a specific carborane compound and having a light output with extremely high efficiency and high luminance. Another object of the present invention is to provide an extremely durable organic light emitting device. It is another object of the present invention to provide an organic light emitting device that is easy to manufacture and can be produced at a relatively low cost.
即ち、本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された一または複数の有機化合物を含む層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が下記一般式［１］〜［１０］で示されるカルボラン化合物の少なくとも一種を含有することを特徴とする。 That is, the organic light-emitting device of the present invention is an organic light-emitting device having at least a layer containing a pair of electrodes composed of an anode and a cathode and one or more organic compounds sandwiched between the pair of electrodes. At least one of the containing layers contains at least one carborane compound represented by the following general formulas [1] to [10].
（式中、Ｒ１〜Ｒ４は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族基または置換あるいは無置換の縮合多環複素環基を表わし、同じであっても異なっていてもよい。 (Wherein R1 to R4 are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted group; Alternatively, it represents an unsubstituted condensed polycyclic heterocyclic group, which may be the same or different.
Ｌは、１乃至２０の整数を表す。） L represents an integer of 1 to 20. )
（式中、Ｒ５〜Ｒ６は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族基または置換あるいは無置換の縮合多環複素環基を表わし、同じであっても異なっていてもよい。 (Wherein R5 to R6 are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted group; Alternatively, it represents an unsubstituted condensed polycyclic heterocyclic group, which may be the same or different.
ｍは、１乃至２０の整数を表す。） m represents an integer of 1 to 20. )
（式中、Ｒ７〜Ｒ８は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族基または置換あるいは無置換の縮合多環複素環基を表わし、同じであっても異なっていてもよい。 Wherein R7 to R8 are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted group Alternatively, it represents an unsubstituted condensed polycyclic heterocyclic group, which may be the same or different.
ｎは、１乃至２０の整数を表す。） n represents an integer of 1 to 20. )
（式中、Ｒ９〜Ｒ１１は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族基または置換あるいは無置換の縮合多環複素環基を表わし、同じであっても異なっていてもよい。 Wherein R9 to R11 are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted group Alternatively, it represents an unsubstituted condensed polycyclic heterocyclic group, which may be the same or different.
Ａｒ１は、置換あるいは無置換のアリーレン基、２価の、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族環基または置換あるいは無置換の縮合多環複素環基を表わす。） Ar1 represents a substituted or unsubstituted arylene group, a divalent substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic ring group, or a substituted or unsubstituted condensed polycyclic heterocyclic group. . )
（式中、Ｒ１２は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族基または置換あるいは無置換の縮合多環複素環基を表わす。 (In the formula, R12 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted group. Represents a substituted fused polycyclic heterocyclic group.
Ａｒ２は、置換あるいは無置換のアリーレン基、２価の、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族環基または置換あるいは無置換の縮合多環複素環基を表わす。） Ar2 represents a substituted or unsubstituted arylene group, a divalent substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic ring group, or a substituted or unsubstituted condensed polycyclic heterocyclic group. . )
（式中、Ｒ１３は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族基または置換あるいは無置換の縮合多環複素環基を表わす。 (In the formula, R13 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted group. Represents a substituted fused polycyclic heterocyclic group.
Ａｒ３は、置換あるいは無置換のアリーレン基、２価の、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族環基または置換あるいは無置換の縮合多環複素環基を表わす。） Ar3 represents a substituted or unsubstituted arylene group, a divalent substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic ring group, or a substituted or unsubstituted condensed polycyclic heterocyclic group. . )
（式中、Ｒ１４〜Ｒ１６は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族基または置換あるいは無置換の縮合多環複素環基を表わし、同じであっても異なっていてもよい。 Wherein R14 to R16 are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group or a substituted group Alternatively, it represents an unsubstituted condensed polycyclic heterocyclic group, which may be the same or different.
Ａｒ４は、３価の、置換あるいは無置換の芳香環基、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族環基または置換あるいは無置換の縮合多環複素環基を表わす。） Ar4 represents a trivalent substituted or unsubstituted aromatic ring group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic ring group, or a substituted or unsubstituted condensed polycyclic heterocyclic group. Represent. )
（式中、Ｒ１７は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族基または置換あるいは無置換の縮合多環複素環基を表わす。 (Wherein R17 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted group; Represents a substituted fused polycyclic heterocyclic group.
Ａｒ５は、３価の、置換あるいは無置換の芳香環基、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族環基または置換あるいは無置換の縮合多環複素環基を表わす。） Ar5 represents a trivalent substituted or unsubstituted aromatic ring group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic ring group, or a substituted or unsubstituted condensed polycyclic heterocyclic group. Represent. )
（式中、Ｒ１８は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族基または置換あるいは無置換の縮合多環複素環基を表わす。 (In the formula, R18 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic group, or a substituted or unsubstituted group. Represents a substituted fused polycyclic heterocyclic group.
Ａｒ６は、３価の、置換あるいは無置換の芳香環基、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族環基または置換あるいは無置換の縮合多環複素環基を表わす。） Ar6 is a trivalent substituted or unsubstituted aromatic ring group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic ring group, or a substituted or unsubstituted condensed polycyclic heterocyclic group. Represent. )
（式中、Ａｒ７は、置換あるいは無置換のアリーレン基、２価の、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族環基または置換あるいは無置換の縮合多環複素環基を表わす。 (In the formula, Ar7 represents a substituted or unsubstituted arylene group, a divalent substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic ring group, or a substituted or unsubstituted condensed polycyclic heterocyclic group. Represents a ring group.
ｐは、２乃至５の整数を表す。） p represents an integer of 2 to 5. )
上記一般式［１］〜［１０］で示されるカルボラン化合物を用いた有機発光素子は、低い印加電圧で高輝度な発光が得られ、耐久性にも優れている。特に本発明のカルボラン化合物を含有する有機層は、電子輸送層として優れている。 The organic light emitting device using the carborane compound represented by the general formulas [1] to [10] can emit light with high luminance at a low applied voltage, and has excellent durability. In particular, the organic layer containing the carborane compound of the present invention is excellent as an electron transport layer.
以下、本発明を詳細に説明する。 Hereinafter, the present invention will be described in detail.
上記一般式［１］〜［１０］で示されるカルボラン化合物は、２個の炭素原子と１０個のボラン原子からなる球状化合物を基本骨格として有する。例えば、一般式［２］で示されるカルボラン化合物のｍ＝１は、Ｃ2Ｈ10Ｂ10Ｒ５Ｒ６の分子式で表せる。 The carborane compounds represented by the general formulas [1] to [10] have a spherical compound composed of two carbon atoms and ten borane atoms as a basic skeleton. For example, m = 1 of the carborane compound represented by the general formula [2] can be represented by a molecular formula of C 2 H 10 B 10 R5R6.
一般式［１］〜［１０］における置換基の具体例を以下に示す。 Specific examples of the substituents in the general formulas [1] to [10] are shown below.
アルキル基としては、メチル基、エチル基、ｎ−プロピル基、ｉｓｏ−プロピル基、ｎ−ブチル基、ｔｅｒ−ブチル基、オクチル基などが挙げられる。 Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a ter-butyl group, and an octyl group.
アリール基としては、フェニル基、ビフェニル基、ターフェニル基などが挙げられる。 Examples of the aryl group include a phenyl group, a biphenyl group, and a terphenyl group.
複素環基としては、チエニル基、ピロリル基、ピリジル基、ビピリジル基、ターピリジル基、オキサゾリル基、オキサジアゾリル基、チアゾリル基、チアジアゾリル基、ターチエニル基などが挙げられる。 Examples of the heterocyclic group include thienyl group, pyrrolyl group, pyridyl group, bipyridyl group, terpyridyl group, oxazolyl group, oxadiazolyl group, thiazolyl group, thiadiazolyl group, and tertenyl group.
縮合多環芳香族基としては、フルオレニル基、ナフチル基、フルオランテニル基、アンスリル基、フェナンスリル基、ピレニル基、テトラセニル基、ペンタセニル基、トリフェニレニル基、ペリレニル基などが挙げられる。 Examples of the condensed polycyclic aromatic group include a fluorenyl group, a naphthyl group, a fluoranthenyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a tetracenyl group, a pentacenyl group, a triphenylenyl group, and a perylenyl group.
縮合多環複素環基としては、カルバゾリル基、フェナントロリル基、ジアザフルオレニル基、アクリジニル基などが挙げられる。 Examples of the condensed polycyclic heterocyclic group include a carbazolyl group, a phenanthroyl group, a diazafluorenyl group, and an acridinyl group.
アリーレン基としては、フェニレン基、ビフェニレン基、ターフェニレン基、ビピリジレン基、ターピリジレン基、フルオレニレン基、フェナントロレニレン基などが挙げられる。 Examples of the arylene group include a phenylene group, a biphenylene group, a terphenylene group, a bipyridylene group, a terpyridylene group, a fluorenylene group, and a phenanthrolenylene group.
上記置換基が有してもよい置換基としては、メチル基、エチル基、プロピル基などのアルキル基、フェニル基、ビフェニル基などのアリール基、チエニル基、ピロリル基、ピリジル基などの複素環基、フルオレニル基、ナフチル基、フルオランテニル基、アンスリル基、フェナンスリル基、ピレニル基、テトラセニル基、ペンタセニル基、トリフェニレニル基、ペリレニル基などの縮合多環芳香族基、カルバゾリル基、フェナントロリル基、ジアザフルオレニル基、アクリジニル基などの縮合多環複素環基、ジメチルアミノ基、ジエチルアミノ基、ジベンジルアミノ基、ジフェニルアミノ基、ジトリルアミノ基、ジアニソリルアミノ基などのアミノ基、メトキシル基、エトキシル基、プロポキシル基、フェノキシル基などのアルコキシル基、シアノ基、フッ素、塩素、臭素、ヨウ素などのハロゲン原子などが挙げられる。 Examples of the substituent that the substituent may have include an alkyl group such as a methyl group, an ethyl group, and a propyl group, an aryl group such as a phenyl group and a biphenyl group, a heterocyclic group such as a thienyl group, a pyrrolyl group, and a pyridyl group. , Fluorenyl group, naphthyl group, fluoranthenyl group, anthryl group, phenanthryl group, pyrenyl group, tetracenyl group, pentacenyl group, triphenylenyl group, perylenyl group and other condensed polycyclic aromatic groups, carbazolyl group, phenanthryl group, diazafur Condensed polycyclic heterocyclic groups such as oleenyl group and acridinyl group, dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, ditolylamino group, amino group such as dianisolylamino group, methoxyl group, ethoxyl group, Alkoxyl groups such as propoxyl group and phenoxyl group, Anomoto, fluorine, chlorine, bromine, a halogen atom such as iodine.
次に、一般式［１］〜［１０］で示されるカルボラン化合物の代表例を以下に挙げるが、本発明はこれらに限定されるものではない。 Next, typical examples of the carborane compounds represented by the general formulas [1] to [10] are listed below, but the present invention is not limited thereto.
一般式（１）で示されるカルボラン化合物 Carborane compound represented by general formula (1)
一般式（２）で示されるカルボラン化合物 Carborane compound represented by general formula (2)
一般式（３）で示されるカルボラン化合物 Carborane compound represented by general formula (3)
一般式（４）で示されるカルボラン化合物 Carborane compound represented by general formula (4)
一般式（５）で示されるカルボラン化合物 Carborane compound represented by general formula (5)
一般式（６）で示されるカルボラン化合物 Carborane compound represented by general formula (6)
一般式（７）で示されるカルボラン化合物 Carborane compound represented by general formula (7)
一般式（８）で示されるカルボラン化合物 Carborane compound represented by general formula (8)
一般式（９）で示されるカルボラン化合物 Carborane compound represented by general formula (9)
一般式（１０）で示されるカルボラン化合物 Carborane compound represented by general formula (10)
一般式［１］〜［１０］で示されるカルボラン化合物は、一般的に知られている方法で合成でき、例えば、
Ｒ．Ｋｏｓｔｅｒ，Ｈｏｕｂｅｎ−Ｗｅｙｌ Ｍｅｔｈｏｄｅｎ ｄｅｒ Ｏｒｇａｎｉｓｃｈｅｎ Ｃｈｅｍｉｅ，Ｏｒｇａｎｏｂｏｒ Ｖｅｒｂｉｎｄｕｎｇｅｎ ＩＩＩ，Ｂａｎｄ ＸＩＩＩ／３ｃ，Ｇｅｏｇ Ｔｈｉｅｍｅ Ｖｅｒｌａｇ，Ｓｔｕｔｔｇａｒｔ，１９８４．
Ｒ．Ｎ．Ｇｒｉｍｅｓ，Ｃａｒｂｏｒａｎｅｓ，Ａｃａｄｅｍｉｃ Ｐｒｅｓｓ，Ｎｅｗ Ｙｏｒｋ，１９７０．
Ｗ．Ｓｉｅｂｅｒｔ，Ａｄｖａｎｃｅｓ ｉｎ Ｂｏｒｏｎ Ｃｈｅｍｉｓｔｒｙ，１９９７．
Ｍａｒｋ Ａ．Ｆｏｘ，Ｊｏｕｒｎａｌ ｏｆ Ｍａｔｅｒｉａｌｓ Ｃｈｅｍｉｓｔｒｙ，２００２，１２，１３０１−１３０６．
などに記載の方法でカルボラン化合物中間体を得ることができる。
The carborane compounds represented by the general formulas [1] to [10] can be synthesized by a generally known method, for example,
R. Koster, Houben-Weyl Method der Organischen Chemie, Organobor Verbundungen III, Band XIII / 3c, Geog Thieme Verlag, Stuttgart, 1984.
R. N. Grimes, Carbonares, Academic Press, New York, 1970.
W. Siebert, Advances in Boron Chemistry, 1997.
Mark A. Fox, Journal of Materials Chemistry, 2002, 12, 1301-1306.
A carborane compound intermediate can be obtained by the method described in the above.
さらにパラジウム触媒を用いたＳｕｚｕｋｉ Ｃｏｕｐｌｉｎｇ法（例えばＣｈｅｍ．Ｒｅｖ．１９９５，９５，２４５７．）、ニッケル触媒を用いたＹａｍａｍｏｔｏ法（例えばＢｕｌｌ．Ｃｈｅｍ．Ｓｏｃ．Ｊｐｎ．，５１，２０９１，１９７８．）などの合成法でカルボラン化合物を得ることができる。 Further, Suzuki Coupling method using a palladium catalyst (for example, Chem. Rev. 1995, 95, 2457.), Yamamoto method using a nickel catalyst (for example, Bull. Chem. Soc. Jpn., 51, 2091, 1978.), etc. A carborane compound can be obtained by a synthesis method.
一般式［１］〜［１０］で示されるカルボラン化合物は、従来の化合物に比べ電子輸送性および耐久性の優れた化合物であり、有機発光素子の有機化合物を含む層、特に、電子輸送層として有用であり、また真空蒸着法や溶液塗布法などによって形成した層は結晶化などが起こりにくく経時安定性に優れている。 The carborane compounds represented by the general formulas [1] to [10] are compounds having excellent electron transport properties and durability as compared with conventional compounds, and include a layer containing an organic compound of an organic light emitting device, particularly as an electron transport layer. It is useful, and a layer formed by a vacuum vapor deposition method or a solution coating method is hardly crystallized and has excellent temporal stability.
本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に狭持された一または複数の有機化合物を含む層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が、一般式［１］〜［１０］で示されるカルボラン化合物の少なくとも一種を含有することを特徴とする。 The organic light-emitting device of the present invention includes the organic compound in an organic light-emitting device having at least a layer including a pair of electrodes composed of an anode and a cathode and one or more organic compounds sandwiched between the pair of electrodes. At least one of the layers contains at least one carborane compound represented by the general formulas [1] to [10].
本発明の有機発光素子においては、一般式［１］〜［１０］で示されるカルボラン化合物を真空蒸着法や溶液塗布法により陽極及び陰極の間に形成する。その有機層の厚みは１０μｍより薄く、好ましくは０．５μｍ以下、より好ましくは０．０１〜０．５μｍの厚みに薄膜化することが好ましい。 In the organic light-emitting device of the present invention, the carborane compound represented by the general formulas [1] to [10] is formed between the anode and the cathode by a vacuum deposition method or a solution coating method. The thickness of the organic layer is less than 10 μm, preferably 0.5 μm or less, more preferably 0.01 to 0.5 μm.
図１〜図６に本発明の有機発光素子の好ましい例を示す。 1 to 6 show preferred examples of the organic light emitting device of the present invention.
図１は本発明の有機発光素子の一例を示す断面図である。図１は基板１上に陽極２、発光層３及び陰極４を順次設けた構成のものである。ここで使用する発光素子はそれ自体でホール輸送能、エレクトロン輸送能及び発光性の性能を単一で有している場合や、それぞれの特性を有する化合物を混ぜて使う場合に有用である。
FIG. 1 is a cross-sectional view showing an example of the organic light emitting device of the present invention. FIG. 1 shows a structure in which an
図２は本発明の有機発光素子における他の例を示す断面図である。図２は基板１上に陽極２、ホール輸送層５、電子輸送層６及び陰極４を順次設けた構成のものである。この場合は発光物質はホール輸送性かあるいは電子輸送性のいづれかあるいは両方の機能を有している材料をそれぞれの層に用い、発光性の無い単なるホール輸送物質あるいは電子輸送物質と組み合わせて用いる場合に有用である。また、この場合、発光層はホール輸送層５あるいは電子輸送層６のいづれかから成る。
FIG. 2 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 2 shows a configuration in which an
図３は本発明の有機発光素子における他の例を示す断面図である。図３は基板１上に陽極２、ホール輸送層５、発光層３，電子輸送層６及び陰極４を順次設けた構成のものである。これはキャリヤ輸送と発光の機能を分離したものであり、ホール輸送性、電子輸送性、発光性の各特性を有した化合物と適時組み合わせて用いられ極めて材料選択の自由度が増すとともに、発光波長を異にする種々の化合物が使用できるため、発光色相の多様化が可能になる。さらに、中央の発光層３に各キャリヤあるいは励起子を有効に閉じこめて発光効率の向上を図ることも可能になる。
FIG. 3 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 3 shows a structure in which an
図４は本発明の有機発光素子における他の例を示す断面図である。図４は図３に対してホール注入層７を陽極２側に挿入した構成であり、陽極２とホール輸送層５の密着性改善あるいはホールの注入性改善に効果があり、低電圧化に効果的である。
FIG. 4 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 4 shows a structure in which a
図５および図６は本発明の有機発光素子における他の例を示す断面図である。図５および図６は、図３および図４に対してホールあるいは励起子（エキシトン）を陰極４側に抜けることを阻害する層（ホール／エキシトンブロッキング層８）を、発光層３、電子輸送層６間に挿入した構成である。イオン化ポテンシャルの非常に高い化合物をホール／エキシトンブロッキング層８として用いる事により、発光効率の向上に効果的な構成である。
5 and 6 are cross-sectional views showing other examples of the organic light-emitting device of the present invention. 5 and FIG. 6 show a layer (hole / exciton blocking layer 8) that prevents holes or excitons (excitons) from passing to the
ただし、図１〜図６はあくまでごく基本的な素子構成であり、本発明の化合物を用いた有機発光素子の構成はこれらに限定されるものではない。例えば、電極と有機層界面に絶縁性層を設ける、接着層あるいは干渉層を設ける、ホール輸送層がイオン化ポテンシャルの異なる２層から構成されるなど多様な層構成をとることができる。 However, FIGS. 1 to 6 are very basic device configurations, and the configuration of the organic light-emitting device using the compound of the present invention is not limited thereto. For example, various layer configurations such as providing an insulating layer at the interface between the electrode and the organic layer, providing an adhesive layer or interference layer, and the hole transporting layer are composed of two layers having different ionization potentials can be employed.
一般式［１］〜［１０］で示されるカルボラン化合物は、従来の化合物に比べ電子輸送性の優れた化合物であり、図１〜図６のいずれの形態でも使用することができる。特に、本発明のカルボラン化合物を用いた有機層は、電子輸送層として有用であり、また真空蒸着法や溶液塗布法などによって形成した層は結晶化などが起こりにくく経時安定性に優れている。 The carborane compounds represented by the general formulas [1] to [10] are compounds having an excellent electron transporting property as compared with conventional compounds, and can be used in any of the forms shown in FIGS. In particular, an organic layer using the carborane compound of the present invention is useful as an electron transport layer, and a layer formed by a vacuum vapor deposition method, a solution coating method, or the like hardly causes crystallization and has excellent temporal stability.
本発明は、電子輸送層の構成成分として一般式［１］〜［１０］で示されるカルボラン化合物を用いるものであるが、これまで知られているホール輸送性化合物、発光性化合物あるいは電子輸送性化合物などを必要に応じて一緒に使用することもできる。 In the present invention, the carborane compound represented by the general formulas [1] to [10] is used as a constituent component of the electron transport layer. The hole transport compound, the luminescent compound, or the electron transport property known so far are used. A compound etc. can also be used together as needed.
以下にこれらの化合物例を挙げる。 Examples of these compounds are given below.
本発明の有機発光素子において、一般式［１］〜［１０］で示されるカルボラン化合物を含有する層および他の有機化合物を含有する層は、一般には真空蒸着法あるいは、適当な溶媒に溶解させて塗布法により薄膜を形成する。特に塗布法で成膜する場合は、適当な結着樹脂と組み合わせて膜を形成することもできる。 In the organic light-emitting device of the present invention, the layer containing the carborane compound represented by the general formulas [1] to [10] and the layer containing another organic compound are generally dissolved in a vacuum deposition method or an appropriate solvent. A thin film is formed by a coating method. In particular, when a film is formed by a coating method, the film can be formed in combination with an appropriate binder resin.
上記結着樹脂としては広範囲な結着性樹脂より選択でき、たとえばポリビニルカルバゾール樹脂、ポリカーボネート樹脂、ポリエステル樹脂、ポリアリレート樹脂、ポリスチレン樹脂、アクリル樹脂、メタクリル樹脂、ブチラール樹脂、ポリビニルアセタール樹脂、ジアリルフタレート樹脂、フェノール樹脂、エポキシ樹脂、シリコーン樹脂、ポリスルホン樹脂、尿素樹脂等が挙げられるが、これらに限定されるものではない。また、これらは単独または共重合体ポリマーとして１種または２種以上混合してもよい。 The binder resin can be selected from a wide range of binder resins such as polyvinyl carbazole resin, polycarbonate resin, polyester resin, polyarylate resin, polystyrene resin, acrylic resin, methacrylic resin, butyral resin, polyvinyl acetal resin, diallyl phthalate resin. , Phenol resin, epoxy resin, silicone resin, polysulfone resin, urea resin and the like, but are not limited thereto. Moreover, you may mix these 1 type, or 2 or more types as a single or copolymer polymer.
陽極材料としては仕事関数がなるべく大きなものがよく、例えば、金、白金、ニッケル、パラジウム、コバルト、セレン、バナジウム等の金属単体あるいはこれらの合金、酸化錫、酸化亜鉛、酸化錫インジウム（ＩＴＯ），酸化亜鉛インジウム等の金属酸化物が使用できる。また、ポリアニリン、ポリピロール、ポリチオフェン、ポリフェニレンスルフィド等の導電性ポリマーも使用できる。これらの電極物質は単独で用いてもよく、複数併用することもできる。 As the anode material, a material having a work function as large as possible is good. For example, simple metals such as gold, platinum, nickel, palladium, cobalt, selenium, vanadium or alloys thereof, tin oxide, zinc oxide, indium tin oxide (ITO), A metal oxide such as zinc indium oxide can be used. In addition, conductive polymers such as polyaniline, polypyrrole, polythiophene, and polyphenylene sulfide can also be used. These electrode materials may be used alone or in combination.
一方、陰極材料としては仕事関数の小さなものがよく、リチウム、ナトリウム、カリウム、セシウム、カルシウム、マグネシウム、アルミニウム、インジウム、銀、鉛、錫、クロム等の金属単体あるいは複数の合金として用いることができる。酸化錫インジウム（ＩＴＯ）等の金属酸化物の利用も可能である。また、陰極は一層構成でもよく、多層構成をとることもできる。 On the other hand, the cathode material preferably has a small work function, and can be used as a single metal or a plurality of alloys such as lithium, sodium, potassium, cesium, calcium, magnesium, aluminum, indium, silver, lead, tin, and chromium. . A metal oxide such as indium tin oxide (ITO) can also be used. Further, the cathode may have a single layer structure or a multilayer structure.
本発明で用いる基板としては、特に限定するものではないが、金属製基板、セラミックス製基板等の不透明性基板、ガラス、石英、プラスチックシート等の透明性基板が用いられる。また、基板にカラーフィルター膜、蛍光色変換フィルター膜、誘電体反射膜などを用いて発色光をコントロールする事も可能である。 Although it does not specifically limit as a board | substrate used by this invention, Transparent substrates, such as opaque board | substrates, such as a metal board | substrate and a ceramic board | substrate, glass, quartz, a plastic sheet, are used. It is also possible to control the color light by using a color filter film, a fluorescent color conversion filter film, a dielectric reflection film, or the like on the substrate.
なお、作成した素子に対して、酸素や水分等との接触を防止する目的で保護層あるいは封止層を設けることもできる。保護層としては、ダイヤモンド薄膜、金属酸化物、金属窒化物等の無機材料膜、フッソ樹脂、ポリパラキシレン、ポリエチレン、シリコーン樹脂、ポリスチレン樹脂等の高分子膜さらには、光硬化性樹脂等が挙げられる。また、ガラス、気体不透過性フィルム、金属などをカバーし、適当な封止樹脂により素子自体をパッケージングすることもできる。 Note that a protective layer or a sealing layer can be provided on the prepared element for the purpose of preventing contact with oxygen or moisture. Examples of the protective layer include diamond thin films, inorganic material films such as metal oxides and metal nitrides, polymer films such as fluorine resin, polyparaxylene, polyethylene, silicone resin, polystyrene resin, and photo-curing resins. It is done. Further, it is possible to cover glass, a gas impermeable film, a metal, etc., and to package the element itself with an appropriate sealing resin.
以下、実施例により本発明をさらに具体的に説明していくが、本発明はこれらに限定されるものではない。 EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples.
＜合成例１＞［例示化合物Ｎｏ．５の合成］ <Synthesis Example 1> [Exemplary Compound No. 1] Synthesis of 5]
３００ｍｌ三ツ口フラスコに、カルボラン化合物［１］５．０ｇ（１６．９ｍｍｏｌ）および酢酸１００ｍｌを入れ、次いで濃硝酸５ｍｌ、濃硫酸５ｍｌ、ヨウ素９．４ｇ（３７．１ｍｍｏｌ）を入れ、７０℃で６時間攪拌した後、反応液を氷水に注加し有機層をクロロホルムで抽出し無水硫酸ナトリウムで乾燥後、シリカゲルカラム（ヘキサン＋トルエン展開溶媒）で精製し、ジヨード体［２］を６．７ｇ（収率７２％）得た。 A 300 ml three-necked flask is charged with 5.0 g (16.9 mmol) of carborane compound [1] and 100 ml of acetic acid, followed by 5 ml of concentrated nitric acid, 5 ml of concentrated sulfuric acid, and 9.4 g (37.1 mmol) of iodine at 70 ° C. for 6 hours. After stirring, the reaction solution was poured into ice water, the organic layer was extracted with chloroform, dried over anhydrous sodium sulfate, and purified with a silica gel column (hexane + toluene developing solvent) to obtain 6.7 g (yield) of diiodide [2]. (Rate 72%).
次に、３００ｍｌ三ツ口フラスコに、上記ジヨード体［２］３．０ｇ（５．４７ｍｍｏｌ）、パラジウム触媒０．１９ｇ（０．２７ｍｍｏｌ）およびジエチルエーテル８０ｍｌを入れ、窒素雰囲気中０℃で攪拌下、別途調製した２−ヨード−９，９−ジメチルフルオレン５．３ｇ（１６．４ｍｍｏｌ）、マグネシウム０．４８ｇ（１９．７ｍｍｏｌ）およびジエチルエーテルのグリニヤール試薬を滴下した。室温で１２時間攪拌した後、水を加え有機層をクロロホルムで抽出し無水硫酸ナトリウムで乾燥後、シリカゲルカラム（ヘキサン＋トルエン展開溶媒）で精製し、例示化合物Ｎｏ．５を２．４ｇ（収率６５％）得た。 Next, 3.0 g (5.47 mmol) of the above diiodide [2], 0.19 g (0.27 mmol) of palladium catalyst and 80 ml of diethyl ether were placed in a 300 ml three-necked flask, and the mixture was separately stirred at 0 ° C. in a nitrogen atmosphere. The prepared 2-iodo-9,9-dimethylfluorene (5.3 g, 16.4 mmol), magnesium (0.48 g, 19.7 mmol) and diethyl ether Grignard reagent were added dropwise. After stirring at room temperature for 12 hours, water was added, the organic layer was extracted with chloroform, dried over anhydrous sodium sulfate, and purified with a silica gel column (hexane + toluene developing solvent). 2.4 g (yield 65%) of 5 was obtained.
＜実施例１＞
図３に示す構造の素子を作成した。
<Example 1>
An element having the structure shown in FIG. 3 was prepared.
基板１としてのガラス基板上に、陽極２としての酸化錫インジウム（ＩＴＯ）をスパッタ法にて１２０ｎｍの膜厚で成膜したものを透明導電性支持基板として用いた。これをアセトン、イソプロピルアルコール（ＩＰＡ）で順次超音波洗浄し、次いでＩＰＡで煮沸洗浄後乾燥した。さらに、ＵＶ／オゾン洗浄したものを透明導電性支持基板として使用した。
What formed indium tin oxide (ITO) as an
透明導電性支持基板上に下記構造式で示される化合物のクロロホルム溶液をスピンコート法により３０ｎｍの膜厚で成膜しホール輸送層５を形成した。
A
さらに下記構造式で示されるＩｒ錯体およびＣＢＰ（重量比５：１００）を真空蒸着法により２０ｎｍの膜厚で成膜し発光層３を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
Further, an Ir complex represented by the following structural formula and CBP (weight ratio 5: 100) were formed into a film with a thickness of 20 nm by a vacuum vapor deposition method to form the
さらに例示化合物Ｎｏ．１で示されるカルボラン化合物を真空蒸着法により４０ｎｍの膜厚で成膜し電子輸送層６を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
Furthermore, Exemplified Compound No. The
次に、陰極４として、アルミニウムとリチウム（リチウム濃度１原子％）からなる蒸着材料を用いて、上記有機層の上に真空蒸着法により厚さ５０ｎｍの金属層膜を形成し、さらに真空蒸着法により厚さ１５０ｎｍのアルミニウム層を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は１．０〜１．２ｎｍ／ｓｅｃの条件で成膜した。
Next, a metal layer film having a thickness of 50 nm is formed on the organic layer by a vacuum deposition method using a deposition material composed of aluminum and lithium (lithium concentration: 1 atomic%) as the
さらに、窒素雰囲気中で保護用ガラス板をかぶせ、アクリル樹脂系接着材で封止した。 Further, a protective glass plate was placed in a nitrogen atmosphere and sealed with an acrylic resin adhesive.
この様にして得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ−Ｌｉ電極（陰極４）を負極にして、１０Ｖの直流電圧を印加すると２６．０ｍＡ／ｃｍ2の電流密度で電流が素子に流れ、７５００ｃｄ／ｍ2の輝度で緑色の発光が観測された。 When a 10V DC voltage was applied to the device thus obtained, with an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode, a current density of 26.0 mA / cm 2 was applied. And green light emission was observed at a luminance of 7500 cd / m 2 .
さらに、電流密度を１０．０ｍＡ／ｃｍ2に保ち１００時間電圧を印加したところ、初期輝度１８００ｃｄ／ｍ2から１００時間後１４００ｃｄ／ｍ2と輝度劣化は小さかった。 Further, where a voltage was applied for 100 hours with the current density kept to 10.0 mA / cm 2, after the initial luminance 1,800 cd / m 2 100 hours 1400cd / m 2 and luminance degradation was small.
＜実施例２〜２５＞
例示化合物Ｎｏ．１に代えて、表１に示す例示化合物を用いた他は実施例１と同様に素子を作成し、同様な評価を行った。結果を表１に示す。
<Examples 2 to 25>
Exemplified Compound No. A device was prepared in the same manner as in Example 1 except that the exemplified compounds shown in Table 1 were used in place of 1, and the same evaluation was performed. The results are shown in Table 1.
＜比較例１〜３＞
例示化合物Ｎｏ．１に代えて、下記構造式で示される化合物を用いた他は実施例１と同様に素子を作成し、同様な評価を行った。結果を表１に示す。
<Comparative Examples 1-3>
Exemplified Compound No. A device was prepared in the same manner as in Example 1 except that a compound represented by the following structural formula was used instead of 1, and the same evaluation was performed. The results are shown in Table 1.
＜実施例２６＞
図３に示す構造の素子を作成した。
<Example 26>
An element having the structure shown in FIG. 3 was prepared.
実施例１と同様に、透明導電性支持基板上にホール輸送層５を形成した。
In the same manner as in Example 1, a
さらにクマリンおよびアルミニウムトリスキノリノール（重合比１：２０）を真空蒸着法により２０ｎｍの膜厚で成膜し発光層３を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
Furthermore, coumarin and aluminum triskinolinol (polymerization ratio 1:20) were formed into a film with a thickness of 20 nm by a vacuum deposition method to form the
さらに例示化合物Ｎｏ．２で示されるカルボラン化合物を４０ｎｍの膜厚で成膜し電子輸送層６を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
Furthermore, Exemplified Compound No. The
次に、実施例１と同様にして、陰極４を成膜し、保護用ガラス板で封止した。
Next, in the same manner as in Example 1, a
この様にして得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ−Ｌｉ電極（陰極４）を負極にして、６Ｖの直流電圧を印加すると１８０ｍＡ／ｃｍ2の電流密度で電流が素子に流れ、１５０００ｃｄ／ｍ2の輝度で緑色の発光が観測された。 When a 6V DC voltage was applied to the device obtained in this manner with the ITO electrode (anode 2) as the positive electrode and the Al-Li electrode (cathode 4) as the negative electrode, the current flowed at a current density of 180 mA / cm 2. And emission of green light was observed at a luminance of 15000 cd / m 2 .
さらに、電流密度を１００ｍＡ／ｃｍ2に保ち１００時間電圧を印加したところ、初期輝度６５００ｃｄ／ｍ2から１００時間後４５００ｃｄ／ｍ2と輝度劣化は小さかった。 Further, when a voltage was applied for 100 hours while maintaining the current density at 100 mA / cm 2 , the luminance deterioration was small, from an initial luminance of 6500 cd / m 2 to 4500 cd / m 2 after 100 hours.
＜実施例２７〜４５＞
例示化合物Ｎｏ．２に代えて、表２に示す例示化合物を用いた他は実施例２６と同様に素子を作成し、同様な評価を行った。結果を表２に示す。
<Examples 27 to 45>
Exemplified Compound No. A device was prepared in the same manner as in Example 26 except that the exemplified compounds shown in Table 2 were used in place of 2, and the same evaluation was performed. The results are shown in Table 2.
＜比較例４〜６＞
例示化合物Ｎｏ．２に代えて、比較化合物Ｎｏ．１、２、３を用いた他は実施例２６と同様に素子を作成し、同様な評価を行った。
結果を表２に示す。
<Comparative Examples 4-6>
Exemplified Compound No. In place of Comparative Compound No. 2 A device was prepared in the same manner as in Example 26 except that 1, 2, and 3 were used, and the same evaluation was performed.
The results are shown in Table 2.
１ 基板
２ 陽極
３ 発光層
４ 陰極
５ ホール輸送層
６ 電子輸送層
７ ホール注入層
８ ホール／エキシトンブロッキング層
DESCRIPTION OF
Claims (10)
Ｌは、１乃至２０の整数を表す。） In an organic light-emitting element having at least one layer including an anode and a cathode and a layer including one or more organic compounds sandwiched between the pair of electrodes, at least one of the layers including the organic compound has the following general formula [ 1] An organic light-emitting device comprising at least one of the carborane compounds represented by 1].
L represents an integer of 1 to 20. )
ｍは、１乃至２０の整数を表す。） In an organic light-emitting element having at least one layer including an anode and a cathode and a layer including one or more organic compounds sandwiched between the pair of electrodes, at least one of the layers including the organic compound has the following general formula [ An organic light-emitting device comprising at least one carborane compound represented by the formula [2].
m represents an integer of 1 to 20. )
ｎは、１乃至２０の整数を表す。） In an organic light-emitting element having at least one layer including an anode and a cathode and a layer including one or more organic compounds sandwiched between the pair of electrodes, at least one of the layers including the organic compound has the following general formula [ [3] An organic light-emitting device comprising at least one carborane compound represented by [3].
n represents an integer of 1 to 20. )
Ａｒ１は、置換あるいは無置換のアリーレン基、２価の、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族環基または置換あるいは無置換の縮合多環複素環基を表わす。） In an organic light-emitting element having at least one layer including an anode and a cathode and a layer including one or more organic compounds sandwiched between the pair of electrodes, at least one of the layers including the organic compound has the following general formula [ [4] An organic light-emitting device comprising at least one carborane compound represented by [4].
Ar1 represents a substituted or unsubstituted arylene group, a divalent substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic ring group, or a substituted or unsubstituted condensed polycyclic heterocyclic group. . )
Ａｒ２は、置換あるいは無置換のアリーレン基、２価の、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族環基または置換あるいは無置換の縮合多環複素環基を表わす。） In an organic light-emitting element having at least one layer including an anode and a cathode and a layer including one or more organic compounds sandwiched between the pair of electrodes, at least one of the layers including the organic compound has the following general formula [ [5] An organic light-emitting device comprising at least one carborane compound represented by [5].
Ar2 represents a substituted or unsubstituted arylene group, a divalent substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic ring group, or a substituted or unsubstituted condensed polycyclic heterocyclic group. . )
Ａｒ３は、置換あるいは無置換のアリーレン基、２価の、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族環基または置換あるいは無置換の縮合多環複素環基を表わす。） In an organic light-emitting element having at least one layer including an anode and a cathode and a layer including one or more organic compounds sandwiched between the pair of electrodes, at least one of the layers including the organic compound has the following general formula [ [6] An organic light-emitting device comprising at least one carborane compound represented by [6].
Ar3 represents a substituted or unsubstituted arylene group, a divalent substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic ring group, or a substituted or unsubstituted condensed polycyclic heterocyclic group. . )
Ａｒ４は、３価の、置換あるいは無置換の芳香環基、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族環基または置換あるいは無置換の縮合多環複素環基を表わす。） In an organic light-emitting element having at least one layer including an anode and a cathode and a layer including one or more organic compounds sandwiched between the pair of electrodes, at least one of the layers including the organic compound has the following general formula [ [7] An organic light-emitting device comprising at least one carborane compound represented by [7].
Ar4 represents a trivalent substituted or unsubstituted aromatic ring group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic ring group, or a substituted or unsubstituted condensed polycyclic heterocyclic group. Represent. )
Ａｒ５は、３価の、置換あるいは無置換の芳香環基、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族環基または置換あるいは無置換の縮合多環複素環基を表わす。） In an organic light-emitting element having at least one layer including an anode and a cathode and a layer including one or more organic compounds sandwiched between the pair of electrodes, at least one of the layers including the organic compound has the following general formula [ [8] An organic light-emitting device comprising at least one carborane compound represented by [8].
Ar5 represents a trivalent substituted or unsubstituted aromatic ring group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic ring group, or a substituted or unsubstituted condensed polycyclic heterocyclic group. Represent. )
Ａｒ６は、３価の、置換あるいは無置換の芳香環基、置換あるいは無置換の複素環基、置換あるいは無置換の縮合多環芳香族環基または置換あるいは無置換の縮合多環複素環基を表わす。） In an organic light-emitting element having at least one layer including an anode and a cathode and a layer including one or more organic compounds sandwiched between the pair of electrodes, at least one of the layers including the organic compound has the following general formula [ [9] An organic light-emitting device comprising at least one carborane compound represented by [9].
Ar6 is a trivalent substituted or unsubstituted aromatic ring group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted condensed polycyclic aromatic ring group, or a substituted or unsubstituted condensed polycyclic heterocyclic group. Represent. )
ｐは、２乃至５の整数を表す。） In an organic light-emitting element having at least one layer including an anode and a cathode and a layer including one or more organic compounds sandwiched between the pair of electrodes, at least one of the layers including the organic compound has the following general formula [ [10] An organic light-emitting device comprising at least one carborane compound represented by [10].
p represents an integer of 2 to 5. )
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